Sodium hydride → HCID 69670891, compound

Participants

Reaction Steps

To a solution of 6-fluoro-5-methoxy-2-phenylindole (200 mg) in N,N-dimethylformamide (4.1 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 54 mg) under cooling with ice, and the mixture was stirred at room temperature for 70 minutes. Then a solution of ethyl 2-bromomethylthiazole-4-carboxylate (249 mg) in N,N-dimethylformamide (0.2 mL) was added, and the mixture was stirred at 80° C. for 25 hours. The reaction mixture was allowed to cool to ambient temperature. A saturated aqueous ammonium chloride solution-water (2/1) were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (125 mg).

Provenance & Evidence